From Dylan to Sinatra: Here are the Best Gambling Songs of All Time

Take a look at our list of the best, most iconic, gambling-themed songs in history and you can put together your own Spotify playlist for the next card game.

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Music is the way to the soul, so how do you reach the soul of a gambler? The soul of someone who calls the Vegas Strip their home? The soul of someone who knows when to hold ’em, when to fold ’em and when to walk away? Well, a few of the artists on this list could tell you a thing or two about reaching the gambler’s heart, and it’s not about donating your last chip to them surprisingly. Take a look at our list of the best, most iconic, gambling-themed songs in history and you can put together your own Spotify playlist for the next card game.

“Rambling, Gambling Willie” by Bob Dylan

The man we’re all here for actually had a few songs that at least referenced gambling or otherwise alluded to it, such as Song to Woody, which was a tribute to Woody Guthrie and mentions “walking a road other men have gone down”, which has been interpreted to be about gambling. There is also Brownsville Girl, which mentions references to gambling like “Let’s keep playing cards and toss them on the floor”.

But the most blatant is Dylan’s story of Willie, which is told in Rambling, Gambling Willie. The lyrics follow Willie’s exploits and mention gambling imagery like cards, dice, and chips, until his tragic end at the hands of a furious, losing, poker player.

“The Gambler” by Kenny Rogers

Let’s get the obvious one out of the way first. The greatest, most iconic song about gambling, in concept and imagery, is clearly Kenny Rogers’ The Gambler. Its iconic status is cemented by the fact that it has been covered by many artists over the years including Bob Dylan, Dolly Parton, Glen Campbell, Johnny Cash, and fun.

Even better, it spurred on a series of TV movies based on the character. This started in the 80’s with Kenny Rogers as The Gambler for five subsequent movies.

Pretty impressive for a song that was written in reportedly 15 minutes, according to writer Don Schlitz.

“Viva Las Vegas” by Elvis Presley

Viva Las Vegas is a celebration of the City of Sin, of the city that made Elvis a tenant for the latter half of his life, and the city of gambling. Written for Elvis’ 1964 film of the same name by Doc Pomus and Mort Shuman, it references the glamour of the city as well as the feverish gambling of the time. All of this is epitomised in the opening of the movie that’s performed with dozens of dancers in a set designed to look like the Vegas strip.

Did you know Elvis never actually performed it live in concert? The track itself has surpassed both the movie and the artist, going on to become a reference whenever anyone mentions Vegas. The Friends Vegas special plays it, countless slot machines reference the title and the providers powering the games know how to depict Vegas in all its glamour, and it has been covered by The Killers, Bruce Springsteen and ZZ Top to name but a few.

“Luck Be a Lady” from Guys and Dolls, sung by Frank Sinatra

Frank Sinatra was a man of simple but exquisite taste. Jack Daniels, suits and fedoras, women and gambling. So it only makes sense that one of his most famous songs would combine two of those famous loves: luck and ladies.

Luck Be a Lady tonight is a prayer to the unnamed, unregistered goddess of luck that she’ll be on your side when you roll the dice. The lyrics, written by Frank Loesser for the 1955 musical movie, Guys and Dolls, cleverly mix personifying luck and even taking her out on a date, trying to woo her to be on your side for the next game. It was so clever, in fact, that it was nominated for an Academy Award for the Best Original Song.

“Poker Face” by Lady Gaga

Similarly, Lady Gaga wants to take a girl on a date in this “mega-hit” about bisexuality. The massive song spent 10 weeks at number one as an expression from Lady Gaga about her own experiences with bisexuality. Her “poker face” was used to hide her intentions with her various partners, as well as hiding her male lovers from her female, and there is a lot of gambling imagery that refers to her sexuality, such as “A little gambling is fun when you’re with me”.

She’s not an LGBT icon for nothing.

Honourable mentions:

  • “Roll the Bones” by Rush
  • “Aces High” by Iron Maiden
  • “The Angel and the Gambler” by Iron Maiden
  • “Blackjack” by Ray Charles
  • “Deck of Cards” by Wink Martindale
  • “Tumbling Dice” by The Rolling Stones
  • “The House of the Rising Sun” cover by The Animals
  • “Queen of Hearts” by Juice Newton
  • “Play the Game” by Queen


Hopefully, now you’ve got a robust playlist to stick on Spotify for your next card game. It’s full of different tastes, genres, and decades, so it will undoubtedly have something for everyone but has the gambling throughline to make sure that everyone focuses on their po-po-poker face.



  1. RGW is not close to being Dylan’s best gambling song. Check out Black Diamond Bay. The gambler finally breaks the bank just as the island explodes. Quite some metaphor, that.

  2. Check out Blind Willie McTell’s, “Dying Crapshooter’s Blues”. I believe it blows away any song mentioned above.

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